Press-free garments and methods of manufacture



United States Patent 3,409,387 a PRESS-FREE GARMENTS AND METHODS OF MANUFACTURE Alex F. Gordon, Black Mountain, N.C., assignor to United Merchants and Manufacturers, Inc., New York, N .Y., a corporation of Delaware No Drawing. Filed Apr. 15, 1966, Ser. No. 542,756

. 9 Claims. (Cl. 8116.2)

ABSTRACT OF. THE DISCLOSURE Process for the production of press-free garments which will retain their crease, which includes the steps of impregnating the fabrics from which the garments are produced with an aqueous solution containing an acetal and a synergistic catalyst, the synergistic catalyst comprising an acid salt of a primary aliphatic amine and a quaternary ammonium salt of the formula:

RY-CHzI IRR R X- wherein R is an aliphatic hydrocarbon group containing about twelve to above eighteen carbon atoms, Y is CONH or Q- ,This invention relates to textile finishing procedures in general and more particularly to improved processes for the production of press-free, crease-retaining garments and the products produced thereby.

In recent years, various methods have been developed by the art for treating fabrics so as to impart durable crease characteristics to the fabrics. In the early stages of these developments, processes were discovered which resulted in the so-called wash and wear fabrics, the products thereof requiring little or no ironinglto reset the crease and remove wrinkles after each washing. The standard process for transforming fabrics into wash and wear garments comprises generally initial impregnation of the fabric with a thermosetting resin, drying, and then curing the impregnated fabric by heating to effect cross linking of the resin and fibers. Thereafter, the fabric was washed, cut, sewn and pressed to result in the finished garment.

Further developments in the garment industry soon gave rise to improvements or variation over the abovedefined general process resultingin the so-called permar'rent-press fabrics. In this later development, the fabrics were subjected to an initial impregnation with a thermosetting resin and then dried, as in the wash and wear procedure. However, in the permanent press process, the impregnated fabric, after drying is cut, sewn and pressed to form the completed garment, without washing and prior to curing. Thereafter the finished garment is cured by the use of heat to effect setting or cross-linking of the resin with fibers of the finished garment. This process results in the production of garments which retain their press and remain wrinkle-free even after repeated washings.

While the permanent-press technique has met with general acceptance in the garment industry, and more importantly with consumers, a number of problems have arisen with its use which have precluded universal acceptance and satisfaction of the garments produced by the process. Foremost among these problems or difficulties is that the procedure has not been found suitable for producing garments composed entirely of cotton, particularly so-called light cottons. While some success has been attained by employing fabrics consisting of heavy cottons, i.e., eleven ounces in weight or more, no process has been developed heretofore which will'effect suitable durable crease resistance in fabrics consisting of light cottons.

This problem appears to arise as a result of the thermosetting resins employed heretofore for impregnation of the fabrics as the chemicals employed have affected the tensile strength and durability of the cottons with resultant poor garment wear and discoloration. The resins primarily employed heretofore to impregnate the fabrics, and which have been found deleterious to the cotton, comprise generally the urea-formaldehyde resins, the melamine-formaldehyde resins, certain sulfones and imidazolidones. As pointed out hereinabove, none of these have yielded satisfactory results when working with all-cotton fabrics.

As cotton is one of the most desirable fabrics for garment formation, attempts have been made to circumvent the problems by employing cotton, which is composed of cellulosic fibers, fortified with synthetic fibers such as polyesters and polyamides (nylon). However, it has been found that incorporation of synthetic fibers into cotton in fact does not prevent or eliminate the deteriorative effect of the finish to the cellulosic fibers, but merely serves to mask the deterioration.

A further problem encountered by prior processes is that the extended curing cycles heretofore employed (sixteen minutes or more) have resulted in shade changes of many of the dyed fabrics. This difficulty has been particularly manifest when working with fabrics colored by dispersed dyes as the dye-stuff tends to migrate from the cloth to the wall and other parts of the equipment thus resulting in difficult cleaning and maintenance problems as well as creating shading changes and nonuniform shading. Moreover, these prior processes have not been suitable for producing white cottons by reason of the fact that white garments tend to suffer discoloration and yellowing during the curing operation and subsequent wash and wear period. Another difficulty interrelated to this problem is the expensive equipment required to effect these long curing or setting periods. Another disadvantage resulting from the extended curing cycles of the art is that wash resistance and light fastness properties of the fabric are adversely affected by long, high temperature curing.

Still another disadvantage of processes employed heretofore is that full resin polymerization or cross-linking is not uniformly achieved as the extent and ratio of the interand intra-molecular cross-linking is not subject to effective control.

It is accordingly one object of the present invention to provide processes for producing press-free, creaseretaining garments and the products thereof which obviate the disadvantages heretofore incurred by the art.

A further object of the present invention is to provide an improved process for the production of press-free, crease-retaining garments which retain their durability and tensile strength and are not subject to color variations during production or when subjected to repeated washings during the wear period.

A still further object of the present invention is to provide an improved process for producing garments composed of cellulosic fibers by the impregnation thereof with a special class of a'cetal resins contained in an aqueous solution wherein brief curing cycles are employed to result in cellulosic fabrics having improved tensile, tear and abrasion strength and durability. 1

An even further object of the present invention resides in the provision of a process for the production of pressfree, crease-retaining garments by the impregnation thereof with a resin-forming aqueous solution of acetals containing a synergistic catalyst, wherein substantially complete resin polymerization or cross-linking is achieved with excellent control.

Other objects and advantages of the present invention will become apparent as the detailed description thereof proceeds.

In accordance with the present invention, and in satisfaction of the above objects and advantages, there is provided an improved process for the production of pressfree, crease-retaining garments which comprises impregnating the fabrics with an aqueous solution containing an acetal and a synergistic catalyst, drying the fabric, cutting and sewing to form a desired garment and then curing the garment at an elevated temperature for a short period. Also provided by the present invention are the garment products produced by the novel process.

When proceeding according to the process of the present invention, it has been found that press-free, creaseretaining garments may be produced which do not suffer from the disadvantages of prior garments as enumerated above. It has been found that impregnation of the fabrics with a certain aqueous solution of acetals containing a synergistic catalyst results in the production of garments having a soft, lustrous hand, outstanding strength and durability properties, remain wrinkle-free and are not subject to discoloration either during the curing step or during the wash and wear period.

The novel process of the invention is considered applicable to the several types of fabrics now employed in the textile industry for forming crease-retaining garments including cellulosic and synthetic fibers in general as well as blends of these fibers, such as cotton blended with nylon or polyesters in ratios of about 40% to 60%. However, the present process is considered particularly applicable to fabrics composed solely of cellulosic fibers, sometimes called all-cottons, and this fabric forms a preferred aspect of the present invention. Even more preferred fabrics for use in the present invention are the light-cottons, or the all-cotton fabrics of less than about eleven ounces in weight. Such light cotton fabrics are eminently suitable for forming garments such as shirts, blouses, and the like, which havenot been successfully commercially produced heretofore because of the processing problems enumerated hereinabove.

In carrying out the process of the invention, the selected fabrics are initially treated or impregnated with an aqueous solution containing (A) an acetal or mixture of acetals as hereinafter defined and (B) a synergistic catalyst mixture constituted of (1) an acid salt of a primary aliphatic amine of the following formula:

wherein R is an alkyl or aryl-alkyl group of one to about eight carbon atoms and HX is a strong acid; and (2) a quaternary ammonium salt of the following formula:

wherein R is an aliphatic hydrocarbon having about twelve 4 to about eighteen carbon atoms which can be normal or branch-chained, Y is CONH or O- mam is an aliphatic tertiary amine cation or a heterocyclic tertiary amine cation, such as dialkylaniline, trialkylamine, pyridine, quinoline, picoline, or homologs of these compounds, such as alkyl-pyridines, quinolines, picolines, etc., and X- is a halogen anion, preferably chlorine or bromine or a mineral acid radical.

This synergistic catalyst mixture may also contain a third (3) catalyst constituent if desired, namely a salt, e.g., a! halide, oxyhalide, nitrate, sulfate, etc., of a metal of Group II, IH or IV of the Periodic Table, or an organic acid, which constituent functions to impart a pH below 7 to the treating solution. Any such water-soluble metallic salt which, when added to water produces a solution having a pH below 7 may be used. Examples of such sa'lts are the alkaline earth metals, e.g., calcium, magnesium, etc., chlorides, nitrates, bromides, chlorates and iodides; aluminum chloride or sulfate boron fluoride, soluble zinc salts including zinc silico fluoride; and zirconium oxychloride. Also, there may be employed instead of, or in conjunction with the metal salt, an organic acid such as citric acid, monochloro acetic acid, formic acid and the like with similar results.

The acetal employed in forming the above aqueous solution comprises the reaction product of an aldehyde with a glycol or polyglycol containing not more than about six carbon atoms in the glycol molecule, the acetal being produced by reaction at least one mole of the aldehyde per mole of glycol. In a preferred embodiment, at least two moles of aldehyde are reacted per mole of glycol. As a general rule, it is preferred to employ as many moles of aldehyde as there are hydroxy groups in the glycol reactant.

The aldehyde reactant employed for producing the acetal includes any material which will function to donate aldehyde radicals under the conditions of the reaction. Such materials include, in addition to formaldehyde per se, paraformaldehyde and other formaldehyde polymers, as Well as acrolein, methacrolein, glyoxal, glutaraldehyde, and the like. The preferred aldehyde is aqueour formaldehyde.

The glycols considered applicable for use in forming the acetals of the present invention by reaction with the aldehyde include the well known glycols or polyglycols containing not more than about six carbon atoms in the glycol molecule and comprise such materials as diethylene glycol, ethylene glycol, propylene glycol, trimethylene glycol, dipentaerythritol, t-ripentaerythritol, etc., as well as glycerol derivatives.

The acetals are prepared by reacting one mole of one of the above defined glycols or glycerols with as many moles of aldehyde as there are hydroxy groups contained in the glycol compound. The preferred acetal for use in forming the aqueous solutions of the invention is pentaerythritol bis acetal of the following formula:

lIgC The acid salts of the primary aliphatic amine identified generally hereinabove [component (1) of synergistic catalyst mixture (B)] include the acid salts of compounds such as monoethanol amine; butanol amine; ethylamine; 2-amino-1-butanol; 2-amino Z-methyl l-propanol; 2- amino-2-methyl-l,3-propanediol; 2 amino-2 ethyl-1,3- propanediol, tris(hydroxy-methyD-amino methane, etc. The strong acids which may be employed to form the acid salts of the above amines include the mineral acids such as hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid and organic acids such as citric acid and the like. The preferred amine salts for use in forming the aqueous solution of the invention is 2-amino-2-methy1-1- propanol hydrochloride, known commercially as Catalyst AC.

The quaternary ammonium component [component (2) above] includes such compounds as stearamide methyl pyridinium chloride; octadecyl oxyr'nethyl pyridinium chloride, oleyloxymethyl pyridinium chloride, stearamide methyl pico'linium chloride, stearamide methyl quinolinium chloride, etc. The preferred quarternary ammonium compound for use in the solution is'stea'ramide methyl pyridinium chloride, sold commercially under the trade name of Zelan AP, chiefly in view of the fact that it is readily available and relatively inexpensive.

The aqueous treating solution prepared employing'the above-identified materials should contain from about 2% to about 16% by weight of the acetal reactant 'on a basis of 100% acetal and not more than about by weight of the synergistic mixture of catalysts with the catalyst components in the mixture present in approximately equal amounts. When operating with or treating cotton fabrics, a solution containing from about 2% to about 10% by weight of the acetal (100%) should be used. When treating rayon or viscose textiles, the acetal content should be from about 4% to about 16% by weight.

When using an aqueous solution containing only catalyst components (1) and (2) above, the amount of the synergistic catalyst mixture should not exceed about 7% or 8% by weight based on the total weight of the treating solution. Preferably the solution should contain from about 0.5% to about 2% of each of the catalyst components (1) and (2) and if component (3) is also used, as preferred, it is employed in the amount of about 1.5% by weight to about 2.5% by weight of the aqueous solution.

The treating solution may also contain additives such as a small amount, for example, of from 0.1% to about 5% by weight, of a buffer to minimize degradation of cellulose fibers due to the acid catalyst. Examples of such buffers include melamine formaldehyde, triazine urea formaldehyde resins (Aerotex 23), dimethylol ethylene urea, dimethylol dihydroxy ethylene urea,-dimethylol propylene urea, dicyandiamide (DCY) and the like. The

solution can also contain esters 'of stearylalcohol and melamine formaldehyde (Permel B sold by American Cyanamid Company) or a mixture of two or more such bulfers and from about 0.5% to about 4% of glycerin, glucose or sorbitol which serves to protect the cellulose and acetal in the treating solution during the early stages of the processing while the acetal is chiefly in the liquid phase. The solution may also contain if desired suitable textile softeners as well as suitable deodorants.

The above aqueous solution isformed to serve as a padding or impregnating bath for the fabrics which are ultimately to be formed into garments. In a preferred embodiment, the bath employed for applying the treating solution is prepared by mixing a portion of the water with the acetal and the other constituents are added in solution form to the water-acetal mixture. The quaternary ammonium salt component is preferably added by dissolving in hot water at a temperature of about 160 F. and added to the solution. The remaining constituents, if not soluble in water atroomtemperature above about 70 F, are dissolved in water at an elevated temperature below the boiling point of the water and added thusly. The temperature of the resultant bath will depend on the particular constitutents employed and should be such that all constituents remain in solution. Anytempera ture below the boiling point. of water can be used. As a practical matter, however, temperatures near room temperature or a few degrees above room temperature for example, from 70 F. to about 110 F., should be employed.

In alternative procedures for impregnating the fabrics with the treating solution, the latter may be sprayed, printed, padded or otherwise applied to impregnate the textile with the treating solution. By either treating method, however, the wet pick-up should be from about 65% to about by weight based on the weight of the dry textile after extraction of the excess solution.

Before the impregnation of any of the fabrics with the aforementioned aqueous solution, it is preferable to thoroughly wash the fabrics in a suitable aqueous soap solution, including a suitable detergent to remove any starch, gelatine, glucose, dextrine, coloring matter or other impurities which may be present, and subsequent ly rinsing the washed fabrics in clear rinse water.'This procedure is deemed necessary to avoid any undue stiffening of the material.

Following application of the treating solution to the fabric at the desired temperature and extractionof the excess solution so that the wet pick-up is from about 65% to about 85 by weight based 'on the dry weightv of the textile, the fabric is dryed at a temperature maintained substantially below the temperature required to cure,'se't or polymerize the resins on the fabric. That is, the polyme'rization of the resin forming'ingredients of the solution, with which the fabric is impregnated, is deliberately avoided in the method of the invention during the stages of padding stretching, finishing and drying. A preferred temperature range for drying the impregnated fabric has been found to be about 200 F. to about 260 F. for a period of from about 0.5 to about 3 minutes.

One embodiment for impregnating and drying the fabrics comprises winding the fabric onto rolls and then successively and continuously impregnating with the above-described aqueous solution by passing the fabric through a conventional dipping or padding machine, stretching and sizing on a standard tenter frame and simultaneously drying as the fabric passes along the frame. Thereafter, the fabric is finally rolled onto a suitable'drum for transportation to a garment makeup room where the treated fabric is cut, sewn and finished to provide the completed garment for subjection to the final curing step to effect polymerization of the resins in the garment. If desired the fabric may be double-dipped in the above described aqueous solution to insure approximately pick-up of the solution by the fabric. Extraction of excess solution may be effected by passing the impregnated fabrics through rollers operating under forced pressure so as to result in a wet pickup of about 65 %to about 85 based on the dry weight of the fabric.

In the padding or impregnating step including squeezing of the fabric, approximately 65 to 85 preferably 70% by weight of the solution is retained in the fabric as it leaves the padding machine for passage to the tenter frame for stretching and setting to size such as width. Whenever it is desired to impart a mechanical finish to the fabric, a conventional flat nip calendar can be employed in conjunction with the tenter frame, the rolls of the calendar being heated at the drying temperature to effect the mechanical finish. It is to be understood that the drying atmosphere of approximately 200 F. is to be maintained as the fabric is passed along the tenter frame, such drying atmosphere being substantially below the temperature required to cure, set or polymerize the resins impregnated on the fabric.

The final roller upon which the fabric is rolled after passing through the tenter frame and flat nip calendar, if used, may or may not be heated depending upon the degree of crease resistance desired in the fabric and this is dependent upon the type of fabric being processed. It has been found that heating of this final or take-off roller usually serves to effect an increase in the crease resistance of the treated fabrics. It is preferred also to so control the drying of the solution and impregnated fabrics so as to retain approximately about 2% to about 8% of the solution or moisture content over and above the natural moisture of the fabrics. After completion of the impregnation and drying steps, the entire drum or roller with the processed or impregnated fabric, containing the residual moisture content mentioned, is then transferred 7 to a garment preparation location for the usual steps of, garment manufacturing, it being understood that the fabric, as worked upon by the garment makers, contains the unpolymerized or unset resins in the amounts, set forth hereinabove.

After the garments have been completed by the steps of cutting, sewing, and finishing, which may include pleating by a mechanical pleating step if desired, the entire completed garments are subjected to an elevated temperature to effect complete polymerization and setting of the resin in the garments to a water-insoluble state. The cur ing step employed in setting or polymerizing the impregnated resins according to this invention constitutes one of the primary advantages disclosed herein as the impregnated garments are preferably cured at a temperature of about 240 F. to about 350 F. for from about 1 to 10 minutes, preferably about 2 to 5 minutes. For pure cottons the preferred curing temperature is about 300 F. to about 310 F. and for other textiles such as rayons and viscose textiles, the preferred curingconditions are at temperatures of about 320 F. The time required for maintaining these curing conditions to effect complete polymerization is the relatively short period of about 2 to 5 minutes, substantially below the time required in processes employed heretofore. This particularly advantageous short time curing cycle of 2 to 5 minutes represents a significant feature of the process because the shade changes of many dyed fabrics are not adversely affected thereby. Also, the short period used avoids such problems as non-uniform shading as well as shade changes in the dyed garments.

The curing operation may be carried out in a number of ways including the use of the conventional curing oven. However, a significant feature of the present process, employing the impregnant solution disclosed herein, resides in the fact that the curing operation may be carried out merely by the application of a heated press. This includes use of the well known hot-head press, employed generally in dry-cleaning establishments to effect the pressing of garments. It is to be understood, of course, that the press is to be operated under the time and temperature conditions set out hereinabove.

The employment of a hot-head press to effect the curing step of the invention represents a decided advance over previous methods in that it eliminates the necessity for expensive garment-setting ovens employed heretofore. This feature, of course, is a significant commercial advantage as it aids in reducing the overall cost of the process.

It is to be understood, however, that the curing process of this invention, employing the aqueous solution described hereinabove, may also be carried out utilizing other heating devices including ovens known as gasfired types. If such ovens are employed, it is necessary that suitable vents be provided therein for permitting the escape of air as well as the escape of vapors emanating from the heated polymerizable resins. Also, the oven should preferably include a plurality of interiorly mounted thermocouples arranged at various locations within the oven for an accurate indication of temperature in the oven as the temperature employed in curing the garments represents a critical feature of the process.

The garments produced as a result of the process of the invention, as hereinabove described, are characterized by having a soft, silky, lustrous hand, outstanding wash resistance, durability and color retention properties and require no ironing after washing, particularly as compared with similar garments produced heretofore. It is theorized that these improvements are due to the unique synergistic catalyst system employed in accordance with the present invention and described hereinabove.

While the explanation for the improvements effected by the synergistic catalyst system is not fully known, the following explanation, believed to be correct, is given to facilitate a better understanding of the invention.

, catalyst mixture of this invention are believed to cooperate to promote the reaction with optimum yield and with minimum adverse effect on the cellulose. The reaction between the cellulose molecules and the acetal resin is believed to produce acetal cross-linking and. in the case of pentaerythritol, the preferred acetal, it is believed that the cross-links may be represented as follows:

, The reaction between the acetal and the cellulose fibers is considered to take place for the most part during the curing step, as at the curing temperature, the acetal is in its most reactive form. The primary aliphatic amine component starts to decompose at temperatures below 200 F., and provides some hydrogen ions at the drying temperature for minimum reaction. However, the major portion does not decompose to form amine vapors and hydrogen ions until temperatures above 240 F., for example, 240 F. to 350 F., are reached at which point the major reaction occurs.

The primary aliphatic amine recatant [component (1) above] is an important element of the mixture or impregnatin solution as it provides the acidic pH necessary to triggerthe acetal-cellulose reaction. This acidic condition is in the range of about 2.5 and is provided by the decomposition of the amine salt of the curing temperatures, as pointed out above.

The quaternary compound is believed to exercise a desired softening effect on the garment fabric and is also agent promoting, for example, by catalyzing the reaction between the acetal and the cellulose fibers. The presence of the quarternary compound is particularly important during the early stages of the treatment because the presence of the quaternary ammonium compound assures maximum utilization of the acetal compound. The quarternary compound and the primary aliphatic amine together are considered to have a synergistic influence, in terms of overall effect, on the cellulosic textiles, particularly, from the standpoint of imparting to the textiles improved strength and durability properties.

The water soluble metallic salts and/or organic acids employed in the system are considered essential to promote the formation of inter-molecular cross-bonds of the cellulose molecules although the intra-molecular crossbonds are less deteriorative to the cellulose than are the inter-molecular cross-bonds. However, both types of cross-bonds are necessary to provide gooddurability, garment strength and wash and wear performance. Employing a catalyst mixture containing components (1) and (2) above, and not (3), a high dry and wet crease angle can be produced with less deterioration caused by inter-molecular cross-bonds. In other words, the tensile strength is greater, and while the washing and wearing properties are good, they are not as good as is obtained when using a catalyst system containing all three components identified above. As indicated, the use of the latter system results in some loss of tensile strength chiefly because of the formation ofmore inter-molecular cross-bonds. Component (3) therefore, is believed responsible for more deterioration of the physical properties of the cellulose than is component (1) or (2),of the synergistic catalyst mixture. Hence, a proper application of the synergistic catalyst system of this invention permits substantially complete control of the va extent, and ratio of inter and intra-molecular. cross-linksv formed as the resin insolubilizes on the cellulose fibers. This feature, in tur n makes possible the control of the adverse eifectof the aci-diccatalyst onthe cellulose.-

by the process ,of the invention are not subject to discoloration' 'either during thecuringoperation or thereafter and that the dyed cottons retain their color uniformly without suifering shade changes. i I

The following era-triples are given to illustrates the EXAMPLE 1 process of this invention. X

In the following examples, cotton hroadclothjwas omponeht Percent treated with the solutions set forth in the examples. The ee a j, 16 .0 aqueous solution was at room'lteniperaturelm" F.) Aerqt x L V 2.0 when the. cloth was passed therethro'ugh andafte'r passage Glyce in; g} 1.5 through the bits offthe p ad'ding, rollers the fabric in DCY I q "0.25 was l' t w hawetpick-up of about 70% 'based .on Catalyst AC 0.5 the fabric eight. The treated cloth was then dried on Calcium chloride 2.0 the rollers at about 200? E. Q Zelan I i In Examples 1 to 11, inclusive, theacetalwaspenta- Water 75.75 e rythritol bisacetal, employed asa56% soli1tioninwater. f f f j In Eiiamples'12 to 19 inclusive, the acetal was tri- Total ..l 100.00 ethylene glycol acetal employed as a 54% solution in' water andmethanol. The percentage values given'helow 7 EX M v represent the percentages by weight of,56% and 54% 2; Component: I i if Percent solutions respectively, ofthe aeetals based o n the total Acetal i 16.0 weightofthesolution. I Aert itex N i 2.0

The Aeroteri'employed in the examples was used 'in Glycerine Q l 1.5 the form commercially available containing 48% solids DCY 0.25 in an aqueous or aqueous/isopropanol medium. The Catalyst AC -5. 0.5 dimethylol-ethylene urea was in the form of a water Calcium chloride Q 4.0 or waterisopropanol solution containing 48% resin solids. Zelan 2.0 The dimethylol-dihydroxy-ethylene urea was in the form Water 73.75 .Of a 50% -aque0us"solution containing 50%. resin solids. The Zelan wasused-in a concentra ion of 50% solids, Total 100,00 thef restb'eing water. H q a,

Component (1) was Catalyst AC, but the acid salts of EXAMPLE 3 any other primary aliphatic amine having six or less car- Component: Percent bon atoms such as. hydrochloric acid, sulfuric a'cid, e tc., Acetal 16.0 he described above, can be used with similar results. 3 Acrotex 2.0 Component (2) is referred to as -Zelan, the compound Glycerine 1.5 used being stearamide methyl pyrldinium .chloride, al- DCY 0.25 though other quaternary ammonium salts, as hereinabove Catalyst AC 0.5 disclosed, may beusedwith equal results. All pe'rcen- Zinc silico-fluoride 3.0 tages and values given are by weight, based on the weight Zelan 2.0 of the total solution; i Water 74.75

In each of the examples; two-different; cotton fabrics were employed. The first consisted of plain white cotton Total 100.00

Example N o 4 5 6 7 8 9 10 11 Pentaerythritol bis acetal s. 5. 0 8. 0 12. 0 16. 0 4. 0 6. 0 10 0 14. 0 Dimethylol Ethylene Urea 5. 0 6. Dimethylol Dihydroxy Ethylene Urea Glycerin 1. DCY 0. Catalyst AC 0. Methanol Amine HCl Zelan 2. Magnesium Chloride 2 Zirconium Oxychloride Monomagnesium Phosphate.--" 0.3 Pyridinium Methylene bis Oxymethyl chlorlde .0 1. 0 1. 5 Water 84. 30 85 74.25 79.00 88.00 84. 00 86.50 75.50

Example No 12 13 14' 15 16 17 18 19 Triethylene Glycol Acetal 5. 0 8. 0 12. 0 16 0 4. 0 6. 0 10. 0 14. 0 Dimethylol Ethylene Urea 5. 0 6. 0

Dimethylo Dihydroxy Ethylene Urea. 2. 0 8. 0

Glycerin 1. 0 1. 0

DCY 0.2 0. 25 0.5 Catalyst AC 0. 5 0. 5 0 5 0. 5

Methanol Amine HO Zelan 2. 0 2. 0 2. 0 2. 0

Magnesium Chloride. 2.0 2.0 2 0 2 0 Zirconium Oxychlorlde V Mononiagnesium Phosphate g, vPg ygidinium Methylene bis Oxyrnethyl Chlor a er broadcloth whereas the second was a colored cotton fabric dyed with a dispersed blue dye. The purpose of ineluding both plain white and dyed fabrics in the samples was to illustrate the applicability of the process of the invention to both types of materials according to the above disclosure. The results to be achieved by use of After impregnation and drying of the cotton fabrics employing the aqueous solutions set forth in the above examples, the treated fabric-s were cut and sewn into sport shirts. After formation and low temperature pressing of the shirts, they were subjected to the action of a hot-head press for three minutes at 310 F., during this technique was to show that white garments produced which period the setting action of the impregnated resin 1 1 occurred. After removal from the press, thefshir'ts showed a pleasing soft hand 'with good wear resistance and dimensional stability. The finish imparted to the garments was found to withstand repeated'washings' 'and dry cleanings and required no ironing to retain their original unwrinkled shape and creases. r

The shirts produced from the white cotton fabric showed no discoloration or fading at the crease lines or anywhere on the shirts immediately following the curing operation or during the subsequent wash and wear period. The blue shirts formed from the dyed cotton fabric retained their original color uniformly throughout the curing step and wear period thus attesting to the attributes and advantages of the disclosed process. H

It will be understood that other impregnating solutions of the type described hereinabove may be employed in the process of the invention with similar results obtaining. Also, the impregnated fabrics may be cut and sewn into other types of garments such as trousers, blouses and the like, as will be obvious to those skilled in the art.

It 'will be appreciated that this invention is not to be limited to the disclosure set forth hereinabove, butis to be limited only by the appended claims.

What is claimed is:

1. A process for the production of press-free, creaseretaining garments which comprises impregnating the fabrics from which the garments are produced with an aqueous solution containing an acetal and a synergistic catalyst, the synergistic catalyst comprising (a) a mixture of a primary aliphatic amine of the formula:

wherein R is an alkyl group having not more than about six carbon atoms and HX is a strong acid, and (b) a quaternary ammonium salt of the formula:

wherein R is an aliphatic hydrocarbon having from about twelve to about eighteen carbon atoms 12 is selected from the group consisting of aliphatic tertiary amines and heterocyclic tertiary amines, and X- T,is se-' lected from the group consisting of a halogen atom and a. mineral acid radical, drying the impregnated fabric, cutting and sewing to form the desired garment, curing the garment at anelevated temperature and thereafter removing the garment. i v l- I 2. A process according to claim 1 wherein the fabric is composed solely of cotton. f 3. A pro'ces'saccording to claim 1 wherein the acetal is the reaction product of an aldehyde anda glycol. 4. A process according to claim'l wherein the aqueous solution contains an additionalvcatalyst constituent (c)? selected from the group consisting of a' salt of 1) a metal of Group II, III or IV of the Periodic Table and (2) anorg anic acid; which constituent imparts a pH of less than about 7 to the treating solution. v '5. A process according to claim 1 wherein the curing step is carried out at a temperature of about 260 F. to about 350 F. for about 2 to 5 minutes. v v I 6. A process according to claim 4 wherein the acetal reactant is pentaerythritol bis acetal of the formula.

References Cited UNITED STATES PATENTS 3,190,715" 6/1965 Gordon 8-116 NORMAN G. TORCHIN, Primary Examiner. I. CANNON, Assistant Examiner.

UNITED STATES PATENT OFFICE CERTIFICATE OF CORRECTION Patent No. 3,409,387 November 5, 1968 Alex F. Gordon It is certified that error appears in the above identified patent and that said Letters Patent are hereby corrected as shown below:

Column 8, line 32, "recatant" should read reactant Column 9, line ll, "bits" should read bite Column 11, lines 36 to 38, the formula should appear as shown below: 0

RC-NHCH -NR R R x Column 12 line 21, claim reference numeral "4" should read 3 Signed and sealed this 10th day of March 1970.

(SEAL) Attest:

WILLIAM E. SCHUYLER, IR.

Commissioner of Patents Edward M. Fletcher, Jr.

Attesting Officer 

